3-[(2-Methyl-4-oxo-4H-chromen-8-yl)methylene]pentane-2,4-dione → 8-(6-Acetyl-2-amino-4-isopropoxy-7-methyl-5,8-dihydropyrido[2,3-d]pyrimidin-5-yl)-2-methyl-4H-chromen-4-one

HRID 1947252Notes

Reaction equation

HRID 1947252 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[C:9]([C:10](=[O:12])[CH:11]=1)=[CH:8][CH:7]=[CH:6][C:5]=2[CH:13]=[C:14]([C:18](=[O:20])[CH3:19])[C:15](=O)[CH3:16].[CH:21]([O:24][C:25]1[N:30]=[C:29]([NH2:31])[N:28]=[C:27]([NH2:32])[CH:26]=1)([CH3:23])[CH3:22]>C(O)(C)C>[C:18]([C:14]1[CH:13]([C:5]2[CH:6]=[CH:7][CH:8]=[C:9]3[C:4]=2[O:3][C:2]([CH3:1])=[CH:11][C:10]3=[O:12])[C:26]2[C:25]([O:24][CH:21]([CH3:22])[CH3:23])=[N:30][C:29]([NH2:31])=[N:28][C:27]=2[NH:32][C:15]=1[CH3:16])(=[O:20])[CH3:19]

Participants

4

Reactant 2

HCID 591869153-[(2-Methyl-4-oxo-4H-chromen-8-yl)methylene]pentane-2,4-dioneHCID 591869186-Isopropoxypyrimidine-2,4-diamine

Product 1

HCID 248577478-(6-Acetyl-2-amino-4-isopropoxy-7-methyl-5,8-dihydropyrido[2,3-d]pyrimidin-5-yl)-2-methyl-4H-chromen-4-one

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

100 mg (0.37 mmol) of 3-[(2-methyl-4-oxo-4H-chromen-8-yl)methylene]pentane-2,4-dione and 62 mg (0.37 mmol) of 6-isopropoxypyrimidine-2,4-diamine are dissolved in 5 ml of isopropanol and heated under reflux under argon for 2 days. The mixture is filtered and the remaining solid is washed with isopropanol. 80 mg (51% of theory) of the title compound are obtained as a white solid.

Workup

  1. temperatureheated
  2. temperatureunder reflux under argon for 2 days
  3. filtrationThe mixture is filtered
  4. washthe remaining solid is washed with isopropanol

Sources & evidence

ORD record
ord-5810f05e18434fb6aed826c6d102261b
Source dataset
uspto-grants-2013_03
Patent number
US08399471B2

Reaction notes

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